1-Allyl-1H-pyrrole-2-carbaldehyde

Base Information

• Chemical Name: 1-Allyl-1H-pyrrole-2-carbaldehyde
• CAS No.: 101001-68-7
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40449090
• Nikkaji Number: J1.067.322D
• Wikidata: Q82268429
• Mol file: 101001-68-7.mol

Synonyms:1-ALLYL-1H-PYRROLE-2-CARBALDEHYDE;101001-68-7;1-prop-2-enylpyrrole-2-carbaldehyde;1-(prop-2-en-1-yl)-1H-pyrrole-2-carbaldehyde;1-allyl-1H-pyrrole-2-carbaldehyde(SALTDATA: FREE);SCHEMBL30523;1-allyl-2-pyrrolecarbaldehyde;1-allylpyrrole-2-carbaldehyde;DTXSID40449090;PNZWYEBTQGJWJX-UHFFFAOYSA-N;BBL031938;MFCD11505317;STL374051;AKOS000112055;AT30944;SB62122;VS-10867;CS-0118504

Chemical Property of 1-Allyl-1H-pyrrole-2-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.082mmHg at 25°C
• Boiling Point: 226.303°C at 760 mmHg
• Flash Point: 90.665°C
• PSA: 22.00000
• Density: 0.967g/cm³
• LogP: 1.48660
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 135.068413911
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

97% ^*data from raw suppliers

1-Allyl-1H-pyrrole-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1C=CC=C1C=O
• General Description: 1-Allyl-1H-pyrrole-2-carbaldehyde serves as a key intermediate in the synthesis of pyrrolizidines and indolizidines through intramolecular nitrone cycloaddition reactions, enabling the production of both racemic and enantiopure forms of these biologically active alkaloids. Its utility lies in facilitating the construction of complex heterocyclic frameworks with potential antiviral and antitumoral properties, highlighting its importance in medicinal chemistry and alkaloid synthesis.

Technology Process of 1-Allyl-1H-pyrrole-2-carbaldehyde

There total 3 articles about 1-Allyl-1H-pyrrole-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) + allyl bromide (106-95-6) → 1-allyl-1H-pyrrole-2-carbaldehyde (101001-68-7)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; for 8h; Reflux;

DOI:10.1021/jo8014598

Reference yield: 80.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) + 3-chloroprop-1-ene (107-05-1) → 1-allyl-1H-pyrrole-2-carbaldehyde (101001-68-7)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; In sodium hydroxide; toluene; at 70 ℃; for 1h;

DOI:10.1016/S0022-328X(00)00658-6

Reference yield: 51.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) + allyl alcohol (107-18-6) → 1-allyl-1H-pyrrole-2-carbaldehyde (101001-68-7)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In dimethyl sulfoxide; at 100 ℃; for 17h; regioselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202200042

upstream raw materials:

2-pyrrole aldehyde

3-chloroprop-1-ene

allyl bromide

allyl alcohol

Downstream raw materials:

N-<(1-allylpyrrol-2-yl)methylidene>benzenemethanamine N-oxide

Co(octaethylporphyrinate)(C₈H₈NO)

Co(meso-tetraphenylporphyrinate)(C₈H₈NO)

C₁₆H₁₈N₂O

Refernces

Intramolecular cycloadditions of nittones derived from 1-allyl-2- pyrrolecarbaldehyde as a route to racemic and enantiopure pyrrolizidines and indolizidines

10.1021/jo9810415

The research focuses on the synthesis of pyrrolizidines and indolizidines, which are structurally related to biologically active alkaloids, using a novel intramolecular nitrone cycloaddition strategy. The purpose of this study was to develop a method for synthesizing these compounds, which possess a wide range of potent biological activities and are considered promising antiviral and antitumoral agents. The researchers successfully synthesized the target molecules in both racemic and enantiopure forms, demonstrating the potential of nitrones derived from 1-allyl-2-pyrrolecarbaldehyde as useful intermediates in alkaloid synthesis. The conclusions highlighted the accessibility of both racemic and enantiopure molecules and suggested future directions for the synthesis of more functionalized structures and improving the degree of asymmetric induction. Key chemicals used in the process included 1-allyl-2-pyrrolecarbaldehyde, benzylhydroxylamine, (R)-N-(1-phenylethyl)hydroxylamine, and various catalysts and solvents such as Pd/C, toluene, and methanol.

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